Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety
Plant diseases caused by bacteria lead to enormous yield and economic losses in agricultural production. To develop innovative bactericides for controlling plant disease, a series of coumarin-3-carboxylic acid derivatives containing acylhydrazone thioether/sulfoxide were designed and synthesized by...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-01-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223008511 |
| _version_ | 1797390528889749504 |
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| author | Juncheng Liang Xin Fu Jing Zhang Haixin Ding Zhiyuan Xu Huochun Ye Fadi Zhu Chao Yan Xiuhai Gan Gang Feng |
| author_facet | Juncheng Liang Xin Fu Jing Zhang Haixin Ding Zhiyuan Xu Huochun Ye Fadi Zhu Chao Yan Xiuhai Gan Gang Feng |
| author_sort | Juncheng Liang |
| collection | DOAJ |
| description | Plant diseases caused by bacteria lead to enormous yield and economic losses in agricultural production. To develop innovative bactericides for controlling plant disease, a series of coumarin-3-carboxylic acid derivatives containing acylhydrazone thioether/sulfoxide were designed and synthesized by utilizing the principles of bioisosterism and active splicing. The bactericidal activities of these derivatives were subsequently evaluated. The result indicated that E2 exhibited the highest antibacterial activities in vitro against Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Acidovorax citrulli, with EC50 values of 2.97, 1.17, and 1.23 µg/mL, respectively. Moreover, in vivo experiments showed that E2 exhibited robust protective properties against Ralstonia solanacearum, and Acidovorax citrulli, with efficacies of 72.52 % and 63.90 %, respectively, at a concentration of 100 µg/mL, which was comparable to the positive control kasugamycin at the same concentration. Scanning electron microscopy analysis revealed that E2 induced changes in the cellular morphology of Acidovorax citrulli, such as shrinkage and collapse. Subsequent investigation revealed that E2 had the capacity to compromise the structural stability of the bacterial membrane of Ralstonia solanacearum. This study represents the first report on the antibacterial activities of this series of coumarin-3-carboxylic acid derivatives containing the acylhydrazone thioether/single-sulfoxide moiety, and the results suggest that coumarin-3-carboxylic acid derivatives containing the acylhydrazone single-sulfoxide may hold potential as effective antibacterial agents. And coumarin-3-carboxylic acid derivatives exhibited promise as plant bacterial agent to prevent rice bacterial leaf blight, tomato bacterial wilt, and melon bacterial fruit blotch. |
| first_indexed | 2024-03-08T23:12:10Z |
| format | Article |
| id | doaj.art-164983bdb1934eeba53c0f32dcc1aeac |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-03-08T23:12:10Z |
| publishDate | 2024-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-164983bdb1934eeba53c0f32dcc1aeac2023-12-15T07:23:24ZengElsevierArabian Journal of Chemistry1878-53522024-01-01171105389Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moietyJuncheng Liang0Xin Fu1Jing Zhang2Haixin Ding3Zhiyuan Xu4Huochun Ye5Fadi Zhu6Chao Yan7Xiuhai Gan8Gang Feng9National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China; Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China; College of Agriculture, Heilongjiang Bayi Agricultural University, Key Laboratory of Low-carbon Green Agriculture in Northeastern China of Ministry of Agriculture and Rural Affairs, Daqing 163319, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaInstitute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Nanchang 330013, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China; Corresponding authors.Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, China; Corresponding authors.Plant diseases caused by bacteria lead to enormous yield and economic losses in agricultural production. To develop innovative bactericides for controlling plant disease, a series of coumarin-3-carboxylic acid derivatives containing acylhydrazone thioether/sulfoxide were designed and synthesized by utilizing the principles of bioisosterism and active splicing. The bactericidal activities of these derivatives were subsequently evaluated. The result indicated that E2 exhibited the highest antibacterial activities in vitro against Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Acidovorax citrulli, with EC50 values of 2.97, 1.17, and 1.23 µg/mL, respectively. Moreover, in vivo experiments showed that E2 exhibited robust protective properties against Ralstonia solanacearum, and Acidovorax citrulli, with efficacies of 72.52 % and 63.90 %, respectively, at a concentration of 100 µg/mL, which was comparable to the positive control kasugamycin at the same concentration. Scanning electron microscopy analysis revealed that E2 induced changes in the cellular morphology of Acidovorax citrulli, such as shrinkage and collapse. Subsequent investigation revealed that E2 had the capacity to compromise the structural stability of the bacterial membrane of Ralstonia solanacearum. This study represents the first report on the antibacterial activities of this series of coumarin-3-carboxylic acid derivatives containing the acylhydrazone thioether/single-sulfoxide moiety, and the results suggest that coumarin-3-carboxylic acid derivatives containing the acylhydrazone single-sulfoxide may hold potential as effective antibacterial agents. And coumarin-3-carboxylic acid derivatives exhibited promise as plant bacterial agent to prevent rice bacterial leaf blight, tomato bacterial wilt, and melon bacterial fruit blotch.http://www.sciencedirect.com/science/article/pii/S1878535223008511AcylhydrazoneAntibacterial activityCoumarin-3-carboxylic acidRalstonia solanacearumSingle-sulfoxide |
| spellingShingle | Juncheng Liang Xin Fu Jing Zhang Haixin Ding Zhiyuan Xu Huochun Ye Fadi Zhu Chao Yan Xiuhai Gan Gang Feng Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety Arabian Journal of Chemistry Acylhydrazone Antibacterial activity Coumarin-3-carboxylic acid Ralstonia solanacearum Single-sulfoxide |
| title | Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety |
| title_full | Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety |
| title_fullStr | Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety |
| title_full_unstemmed | Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety |
| title_short | Design, synthesis and antibacterial activity of coumarin-3-carboxylic acid derivatives containing acylhydrazone moiety |
| title_sort | design synthesis and antibacterial activity of coumarin 3 carboxylic acid derivatives containing acylhydrazone moiety |
| topic | Acylhydrazone Antibacterial activity Coumarin-3-carboxylic acid Ralstonia solanacearum Single-sulfoxide |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223008511 |
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